annularin B | 628302-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: annularin B
• 英文别名: 2H-Pyran-2-one, 5-(hydroxymethyl)-4-methoxy-6-propyl-；5-(hydroxymethyl)-4-methoxy-6-propylpyran-2-one
• CAS: 628302-55-6
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: ZWMLESXRXFUSQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氧代己酸甲酯 在 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 175.0h， 生成 annularin B
  参考文献：
  名称：

  Total Syntheses of Daldiniapyrone, Annularin B, and (±)-Annularin F

  摘要：

  本文首次对达迪尼亚酮、环烯醚萜醇 B 和环烯醚萜醇 F 进行了简要的全面综述。

  DOI：

  10.1055/s-2006-942355

文献信息

• Cancer cell growth inhibition by black bean (phaseolus vulgaris l) extracts
  申请人：Instituto Tecnologico y de Estudios Superiores de Monterrey

  公开号：EP2311476A2

  公开（公告）日：2011-04-20

  A group of phytochemical compounds extracted from whole germinated or not germinated black beans (Phaseolus vulgaris L) and/or their dry milled fractions such as seed coats or hulls and cotyledons is described. These phytochemicals are classified as phenolics, such as polyphenols, flavonoids, coumarins, and tannins, triterpenes such as saponins, phytosterols and other antioxidant compounds that proved to be effective to decrease cancer proliferation of hormone dependent mammary (MCF-7), hormone independent hepatic (HepG2) and colon (Caco2) cancer cells. They also effectively protect against chemical damage induced with DMBA and furthermore prevented cancer induced by this chemical in Wistar rats and also reduced tumor size when consumed after tumor detection. Methanol, acetone, ethanol, water and mixtures of these solvents were used to obtain the extracts from raw, cooked, and germinated black beans of different varieties, both from the whole grain and the hulls. The black bean malting process produced extracts rich in aglycone forms of the previous mentioned compounds that were more biologically active against MCF-7 cancer cell proliferation. Both raw extracts, C-18 HPLC refined extracts and fractionated extracts may be used in the treatment, prophylaxis, amelioration or defense against a variety of hormone dependent and independent cancers. The extracts and compounds have additional utilities, e.g., lower cholesterol or lower oxidation of LDL and/or inhibit cholesterol synthesis (or the enzyme therefor) and/or reduce liver fibrosis and/or reduce symptoms of menopause and/or stimulate calcium absorption and/or have estrogenic activity such as feminizing estrogenic activity and/or are antioxidants, for instance, as an active ingredient in a nutritional supplement and/or as a food, cosmetic or pharmaceutical antioxidants or colorants.

  本文介绍了从整个发芽或未发芽的黑豆（Phaseolus vulgaris L）和/或其干磨部分（如种皮或种壳和子叶）中提取的一组植物化学物质。这些植物化学物质分为酚类（如多酚、类黄酮、香豆素和单宁）、三萜类（如皂苷）、植物甾醇和其他抗氧化化合物，事实证明它们能有效减少依赖激素的乳腺癌细胞（MCF-7）、不依赖激素的肝癌细胞（HepG2）和结肠癌细胞（Caco2）的癌细胞增殖。它们还能有效抵御 DMBA 诱导的化学损伤，并进一步防止 Wistar 大鼠因这种化学物质而诱发癌症，在检测到肿瘤后食用还能缩小肿瘤大小。研究人员使用甲醇、丙酮、乙醇、水和这些溶剂的混合物，从不同品种的生黑豆、熟黑豆和发芽黑豆（包括整粒黑豆和豆壳）中提取提取物。黑豆发芽过程产生的提取物富含上述化合物的苷元形式，对 MCF-7 癌细胞增殖具有更强的生物活性。生提取物、C-18 HPLC 精炼提取物和分馏提取物均可用于治疗、预防、改善或防御各种激素依赖型和独立型癌症。这些提取物和化合物还具有其他效用，例如，降低胆固醇或降低低密度脂蛋白的氧化和/或抑制胆固醇合成（或其酶）和/或减轻肝纤维化和/或减轻更年期症状和/或刺激钙吸收和/或具有雌激素活性，如雌性化雌激素活性和/或抗氧化剂，例如，作为营养补充剂的活性成分和/或作为食品、化妆品或药品的抗氧化剂或着色剂。
• CANCER CELL GROWTH INHIBITION BY BLACK BEAN (PHASEOLUS VULGARIS L.) EXTRACTS
  申请人：Instituto Tecnologico y de Estudios Superiores de Monterrey

  公开号：EP1750732B1

  公开（公告）日：2013-03-27
• Cancer cell growth inhibition by black bean (Phaseolus vulgaris L) extracts
  申请人：Gutierrez-Uribe Janet A.

  公开号：US20100216729A1

  公开（公告）日：2010-08-26

  A group of phytochemical compounds extracted from whole germinated or not germinated black beans ( Phaseolus vulgaris L) and/or their dry milled fractions such as seed coats or hulls and cotyledons is described. These phytochemicals are classified as phenolics, such as polyphenols, flavonoids, coumarins, and tannins, triterpenes such as saponins, phytosterols and other antioxidant compounds that proved to be effective to decrease cancer proliferation of hormone dependent mammary (MCF-7), hormone independent hepatic (HepG2) and colon (Caco2) cancer cells. They also effectively protect against chemical damage induced with DMBA and furthermore prevented cancer induced by this chemical in Wistar rats and also reduced tumor size when consumed after tumor detection. Methanol, acetone, ethanol, water and mixtures of these solvents were used to obtain the extracts from raw, cooked, and germinated black beans of different varieties, both from the whole grain and the hulls. The black bean malting process produced extracts rich in aglycone forms of the previous mentioned compounds that were more biologically active against MCF-7 cancer cell proliferation. Both raw extracts, C-18 HPLC refined extracts and fractionated extracts may be used in the treatment, prophylaxis, amelioration or defense against a variety of hormone dependent and independent cancers. The extracts and compounds have additional utilities, e.g., lower cholesterol or lower oxidation of LDL and/or inhibit cholesterol synthesis (or the enzyme therefor) and/or reduce liver fibrosis and/or reduce symptoms of menopause and/or stimulate calcium absorption and/or have estrogenic activity such as feminizing estrogenic activity and/or are antioxidants, for instance, as an active ingredient in a nutritional supplement and/or as a food, cosmetic or pharmaceutical antioxidants or colorants.
• US7763292B2
  申请人：——

  公开号：US7763292B2

  公开（公告）日：2010-07-27
• [EN] PHARMACEUTICAL COMPOSITION, PROCESS FOR OBTAINING AND USING SECONDARY METABOLITES PRODUCED BY THE FUNGUS EXSEROHILUM ROSTRATUM IN CELL REGENERATION<br/>[FR] COMPOSITION PHARMACEUTIQUE, PROCÉDÉ D'OBTENTION ET UTILISATION DE MÉTABOLITES SECONDAIRES PRODUITS PAR LE CHAMPIGNON EXSEROHILUM ROSTRATUM DANS LA RÉGÉNÉRATION CELLULAIRE<br/>[PT] COMPOSIÇÃO FARMACÊUTICA, PROCESSO DE OBTENÇÃO E USO DE METABOLITOS SECUNDÁRIOS PRODUZIDO PELO FUNGO EXSEROHILUM ROSTRATUM NA REGENERAÇÃO CELULAR
  申请人：INST BUTANTAN

  公开号：WO2020041851A2

  公开（公告）日：2020-03-05

  A presente invenção se refere a uma composição farmacêutica compreendendo metabólitos secundários produzido pelo fungo Exserohilum rostratum na regeneração celular. Particularmente, a presente invenção se refere a composição farmacêutica compreendendo metabólitos secundários monocerina e anularina I produzidos a partir da cultura do fungo Exserohilum rostratum para regeneração celular. Em outro aspecto, a presente invenção se refere ao processo de obtenção e uso dos referidos metabólitos secundários produzido pelo fungo Exserohilum rostratum na regeneração celular.

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